Hydroxyamine hydrochloride → HCID 86592613, compound

HRID 720265Notes

Reaction equation

HRID 720265 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=O)[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:20][OH:21]>C(O)C>[C:1]([O:5][C:6](=[O:18])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=[N:20][OH:21])[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 58739156HCID 58739156, compound

Product 1

HCID 86592613HCID 86592613, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (s)-[1-(3-formyl-phenyl)-ethyl]-carbamic acid tert-butyl ester (1.5 g, 6 mmol) in ethanol (50 mL) were added hydroxylamine hydrochloride (833 mg, 12 mmol) triethylamine (2.5 mL, 18 mmol), the reaction mixture was heated at reflux for 18 h, and the reaction mixture was cooled down to room temperature and concentrated in vacuo. The crude product was diluted in EtOAc (100 mL) and extracted with 0.5N HCl. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated in vacuo to provide the title compound (1.53 g, 96% yield) as a solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. concentrationconcentrated in vacuo
  4. additionThe crude product was diluted in EtOAc (100 mL)
  5. extractionextracted with 0.5N HCl
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-014f59a9d6ae44539886e4baee82d9e6
Source dataset
uspto-grants-2006_11
Patent number
US07135472B2

Reaction notes

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